#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/42/2224253.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224253
loop_
_publ_author_name
'Asghar, Amina'
'Iqbal, Mohammad S.'
'Tahir, M. Nawaz'
_publ_section_title
;Mutual prodrug of cephazolin and benzydamin:
 3-[(1-benzyl-1H-indazol-3-yl)oxy]-N,N-dimethylpropan-1-aminium
 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate
 (benzydaminium cephazolinate)
;
_journal_coeditor_code           HB5219
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3132
_journal_page_last               o3133
_journal_paper_doi               10.1107/S1600536809047941
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H24 N3 O +, C14 H13 N8 O4 S3 -'
_chemical_formula_moiety         'C19 H24 N3 O +, C14 H13 N8 O4 S3 -'
_chemical_formula_sum            'C33 H37 N11 O5 S3'
_chemical_formula_weight         763.92
_chemical_name_common
;
benzydaminium cephazolinate
;
_chemical_name_systematic
;
3-[(1-Benzyl-1H-indazol-3-yl)oxy]-N,N-\
dimethylpropan-1-aminium
3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-\
[(1H-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]octane-2-\
carboxylate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90.587(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   44.409(3)
_cell_length_b                   7.1777(5)
_cell_length_c                   11.2683(8)
_cell_measurement_reflns_used    3824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.59
_cell_volume                     3591.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.60
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_sigmaI/netI    0.1081
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34321
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut needle'
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.229
_refine_ls_abs_structure_details 'Flack (1983), 2918 Friedal Pairs'
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0504
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                4092
_reflns_number_total             6750
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5219.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2224253
_cod_database_fobs_code          2224253
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,-z
3 1/2+x,1/2+y,z
4 1/2-x,1/2+y,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.14103(6) 0.2863(4) 0.9240(3) 0.0552(11) Uani . . 1.000
N N1 0.18241(7) 0.2542(4) 0.7971(3) 0.0420(12) Uani . . 1.000
N N2 0.19416(7) 0.3698(5) 0.7111(3) 0.0433(12) Uani . . 1.000
N N3 0.06627(7) 0.0749(5) 1.1012(3) 0.0372(11) Uani . . 1.000
C C1 0.15436(8) 0.5181(5) 0.7788(3) 0.0340(12) Uani . . 1.000
C C2 0.13236(9) 0.6570(6) 0.7813(4) 0.0510(17) Uani . . 1.000
C C3 0.13442(11) 0.8000(7) 0.7038(4) 0.0640(17) Uani . . 1.000
C C4 0.15844(11) 0.8115(6) 0.6251(4) 0.0610(19) Uani . . 1.000
C C5 0.18016(10) 0.6769(6) 0.6189(3) 0.0490(17) Uani . . 1.000
C C6 0.17762(8) 0.5263(5) 0.6969(3) 0.0370(12) Uani . . 1.000
C C7 0.21920(9) 0.3080(6) 0.6398(3) 0.0463(17) Uani . . 1.000
C C8 0.24923(8) 0.3866(5) 0.6760(3) 0.0353(12) Uani . . 1.000
C C9 0.25878(9) 0.3855(6) 0.7933(4) 0.0466(17) Uani . . 1.000
C C10 0.28704(10) 0.4478(6) 0.8244(4) 0.0520(17) Uani . . 1.000
C C11 0.30587(9) 0.5147(6) 0.7391(4) 0.0484(17) Uani . . 1.000
C C12 0.29672(9) 0.5182(6) 0.6231(4) 0.0492(17) Uani . . 1.000
C C13 0.26851(9) 0.4546(6) 0.5911(3) 0.0450(17) Uani . . 1.000
C C14 0.15916(9) 0.3469(5) 0.8366(3) 0.0393(16) Uani . . 1.000
C C15 0.14483(9) 0.1004(6) 0.9660(4) 0.0546(17) Uani . . 1.000
C C16 0.12086(10) 0.0662(8) 1.0548(4) 0.0699(19) Uani . . 1.000
C C17 0.09024(9) 0.0869(7) 1.0079(4) 0.0636(19) Uani . . 1.000
C C18 0.06411(12) 0.2420(7) 1.1765(4) 0.089(3) Uani . . 1.000
C C19 0.03700(9) 0.0436(8) 1.0420(4) 0.0718(19) Uani . . 1.000
S S1 0.10575(2) 0.19304(14) 0.49823(9) 0.0428(3) Uani . . 1.000
S S2 0.14745(2) 0.56694(16) 0.18123(9) 0.0463(4) Uani . . 1.000
S S3 0.20738(2) 0.44836(15) 0.08659(9) 0.0456(4) Uani . . 1.000
O O2 0.05024(6) 0.8249(3) 0.3777(2) 0.0384(9) Uani . . 1.000
O O3 0.08047(6) 0.7715(4) 0.2253(2) 0.0547(11) Uani . . 1.000
O O4 0.02066(6) 0.4136(4) 0.3861(2) 0.0405(9) Uani . . 1.000
O O5 0.02552(7) 0.0728(4) 0.7592(2) 0.0587(13) Uani . . 1.000
N N4 0.19862(7) 0.4956(4) 0.3076(3) 0.0406(12) Uani . . 1.000
N N5 0.22865(7) 0.4435(4) 0.2966(3) 0.0427(12) Uani . . 1.000
N N6 0.06812(6) 0.4815(4) 0.4717(2) 0.0279(10) Uani . . 1.000
N N7 0.03965(6) 0.0819(4) 0.5676(2) 0.0315(10) Uani . . 1.000
N N8 0.02949(7) -0.3125(4) 0.7545(3) 0.0325(11) Uani . . 1.000
N N9 0.05801(8) -0.3400(5) 0.7855(3) 0.0603(16) Uani . . 1.000
N N10 0.05818(10) -0.4303(7) 0.8833(4) 0.0751(17) Uani . . 1.000
N N11 0.02978(11) -0.4641(5) 0.9184(3) 0.0663(16) Uani . . 1.000
C C20 0.13044(8) 0.3791(5) 0.4529(3) 0.0440(14) Uani . . 1.000
C C21 0.11584(8) 0.5428(5) 0.3900(3) 0.0317(12) Uani . . 1.000
C C22 0.08645(8) 0.5831(5) 0.3948(3) 0.0293(12) Uani . . 1.000
C C23 0.07099(9) 0.7410(5) 0.3273(3) 0.0330(12) Uani . . 1.000
C C24 0.13782(8) 0.6622(5) 0.3251(3) 0.0396(14) Uani . . 1.000
C C25 0.18490(8) 0.5045(5) 0.2061(3) 0.0376(12) Uani . . 1.000
C C26 0.23635(9) 0.4134(5) 0.1884(3) 0.0407(14) Uani . . 1.000
C C27 0.26722(9) 0.3571(6) 0.1520(4) 0.0570(17) Uani . . 1.000
C C28 0.07883(8) 0.3496(5) 0.5621(3) 0.0347(12) Uani . . 1.000
C C29 0.04609(8) 0.2771(5) 0.5704(3) 0.0323(12) Uani . . 1.000
C C30 0.04024(8) 0.3968(5) 0.4591(3) 0.0289(12) Uani . . 1.000
C C31 0.02943(8) -0.0044(5) 0.6644(3) 0.0340(12) Uani . . 1.000
C C32 0.02179(8) -0.2078(5) 0.6480(3) 0.0337(12) Uani . . 1.000
C C33 0.01254(10) -0.3891(5) 0.8368(4) 0.0479(17) Uani . . 1.000
H H2 0.11664 0.65124 0.83513 0.0612 Uiso . . 1.000
H H3 0.11965 0.89190 0.70279 0.0762 Uiso . . 1.000
H H3N 0.0701(8) -0.035(5) 1.148(3) 0.0446 Uiso . . 1.000
H H4 0.15971 0.91434 0.57520 0.0732 Uiso . . 1.000
H H5 0.19589 0.68514 0.56533 0.0588 Uiso . . 1.000
H H7A 0.21521 0.34164 0.55778 0.0555 Uiso . . 1.000
H H7B 0.22030 0.17314 0.64381 0.0555 Uiso . . 1.000
H H9 0.24592 0.34200 0.85174 0.0560 Uiso . . 1.000
H H10 0.29334 0.44458 0.90336 0.0622 Uiso . . 1.000
H H11 0.32494 0.55774 0.76019 0.0578 Uiso . . 1.000
H H12 0.30960 0.56374 0.56540 0.0593 Uiso . . 1.000
H H13 0.26244 0.45759 0.51190 0.0541 Uiso . . 1.000
H H15A 0.16458 0.08557 1.00236 0.0653 Uiso . . 1.000
H H15B 0.14299 0.01281 0.90075 0.0653 Uiso . . 1.000
H H16A 0.12321 -0.05902 1.08589 0.0837 Uiso . . 1.000
H H16B 0.12364 0.15230 1.12035 0.0837 Uiso . . 1.000
H H17A 0.08661 -0.00932 0.94905 0.0766 Uiso . . 1.000
H H17B 0.08860 0.20648 0.96821 0.0766 Uiso . . 1.000
H H18A 0.05950 0.34834 1.12796 0.1331 Uiso . . 1.000
H H18B 0.08295 0.26181 1.21710 0.1331 Uiso . . 1.000
H H18C 0.04846 0.22478 1.23366 0.1331 Uiso . . 1.000
H H19A 0.03248 0.14682 0.99069 0.1076 Uiso . . 1.000
H H19B 0.02159 0.03237 1.10070 0.1076 Uiso . . 1.000
H H19C 0.03785 -0.06890 0.99605 0.1076 Uiso . . 1.000
H H7N 0.04237 0.01975 0.50338 0.0378 Uiso . . 1.000
H H20A 0.14087 0.42565 0.52288 0.0529 Uiso . . 1.000
H H20B 0.14552 0.32694 0.40083 0.0529 Uiso . . 1.000
H H24A 0.15602 0.67492 0.37270 0.0474 Uiso . . 1.000
H H24B 0.12927 0.78543 0.31426 0.0474 Uiso . . 1.000
H H27A 0.27708 0.29376 0.21663 0.0852 Uiso . . 1.000
H H27B 0.27858 0.46598 0.13134 0.0852 Uiso . . 1.000
H H27C 0.26590 0.27544 0.08474 0.0852 Uiso . . 1.000
H H28 0.08607 0.41003 0.63503 0.0418 Uiso . . 1.000
H H29 0.03622 0.33403 0.63884 0.0385 Uiso . . 1.000
H H32A 0.00044 -0.22075 0.63099 0.0402 Uiso . . 1.000
H H32B 0.03281 -0.25736 0.58121 0.0402 Uiso . . 1.000
H H33 -0.00840 -0.38952 0.83662 0.0575 Uiso . . 1.000
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C20 S1 C28 . . . 93.40(17) no
C24 S2 C25 . . . 100.75(17) no
C25 S3 C26 . . . 87.07(17) no
C14 O1 C15 . . . 118.3(3) no
N2 N1 C14 . . . 103.8(3) no
C6 N2 C7 . . . 127.5(3) no
N1 N2 C6 . . . 111.9(3) no
N1 N2 C7 . . . 120.2(3) no
C17 N3 C18 . . . 114.0(4) no
C17 N3 C19 . . . 108.6(3) no
C18 N3 C19 . . . 108.8(4) no
C17 N3 H3N . . . 108(2) no
C18 N3 H3N . . . 111(2) no
C19 N3 H3N . . . 106(2) no
N5 N4 C25 . . . 112.2(3) no
N4 N5 C26 . . . 113.2(3) no
C22 N6 C30 . . . 133.6(3) no
C22 N6 C28 . . . 125.4(3) no
C28 N6 C30 . . . 94.1(3) no
C29 N7 C31 . . . 120.3(3) no
N9 N8 C32 . . . 120.7(3) no
C32 N8 C33 . . . 131.6(3) no
N9 N8 C33 . . . 107.6(3) no
N8 N9 N10 . . . 107.5(3) no
N9 N10 N11 . . . 110.3(4) no
N10 N11 C33 . . . 105.2(4) no
C29 N7 H7N . . . 120.00 no
C31 N7 H7N . . . 120.00 no
C6 C1 C14 . . . 103.5(3) no
C2 C1 C6 . . . 120.5(3) no
C2 C1 C14 . . . 135.8(4) no
C1 C2 C3 . . . 118.5(4) no
C2 C3 C4 . . . 120.8(4) no
C3 C4 C5 . . . 122.3(4) no
C4 C5 C6 . . . 116.9(4) no
N2 C6 C1 . . . 107.0(3) no
C1 C6 C5 . . . 120.9(3) no
N2 C6 C5 . . . 132.1(3) no
N2 C7 C8 . . . 114.8(3) no
C7 C8 C9 . . . 121.4(3) no
C7 C8 C13 . . . 120.0(3) no
C9 C8 C13 . . . 118.6(3) no
C8 C9 C10 . . . 120.8(4) no
C9 C10 C11 . . . 119.9(4) no
C10 C11 C12 . . . 120.1(4) no
C11 C12 C13 . . . 120.4(4) no
C8 C13 C12 . . . 120.3(3) no
N1 C14 C1 . . . 113.8(3) no
O1 C14 N1 . . . 124.2(3) no
O1 C14 C1 . . . 122.1(3) no
O1 C15 C16 . . . 107.1(4) no
C15 C16 C17 . . . 114.2(4) no
N3 C17 C16 . . . 113.8(4) no
C1 C2 H2 . . . 121.00 no
C3 C2 H2 . . . 121.00 no
C4 C3 H3 . . . 120.00 no
C2 C3 H3 . . . 120.00 no
C3 C4 H4 . . . 119.00 no
C5 C4 H4 . . . 119.00 no
C6 C5 H5 . . . 122.00 no
C4 C5 H5 . . . 122.00 no
N2 C7 H7A . . . 109.00 no
C8 C7 H7B . . . 109.00 no
N2 C7 H7B . . . 109.00 no
C8 C7 H7A . . . 109.00 no
H7A C7 H7B . . . 108.00 no
C10 C9 H9 . . . 120.00 no
C8 C9 H9 . . . 120.00 no
C9 C10 H10 . . . 120.00 no
C11 C10 H10 . . . 120.00 no
C12 C11 H11 . . . 120.00 no
C10 C11 H11 . . . 120.00 no
C13 C12 H12 . . . 120.00 no
C11 C12 H12 . . . 120.00 no
C8 C13 H13 . . . 120.00 no
C12 C13 H13 . . . 120.00 no
O1 C15 H15B . . . 110.00 no
C16 C15 H15A . . . 110.00 no
O1 C15 H15A . . . 110.00 no
H15A C15 H15B . . . 109.00 no
C16 C15 H15B . . . 110.00 no
C15 C16 H16A . . . 109.00 no
C15 C16 H16B . . . 109.00 no
C17 C16 H16B . . . 109.00 no
H16A C16 H16B . . . 108.00 no
C17 C16 H16A . . . 109.00 no
C16 C17 H17A . . . 109.00 no
C16 C17 H17B . . . 109.00 no
H17A C17 H17B . . . 108.00 no
N3 C17 H17B . . . 109.00 no
N3 C17 H17A . . . 109.00 no
N3 C18 H18B . . . 109.00 no
N3 C18 H18A . . . 110.00 no
H18A C18 H18C . . . 109.00 no
N3 C18 H18C . . . 109.00 no
H18A C18 H18B . . . 109.00 no
H18B C18 H18C . . . 109.00 no
N3 C19 H19B . . . 109.00 no
N3 C19 H19C . . . 109.00 no
H19A C19 H19C . . . 109.00 no
H19B C19 H19C . . . 109.00 no
H19A C19 H19B . . . 109.00 no
N3 C19 H19A . . . 109.00 no
S1 C20 C21 . . . 116.6(3) no
C22 C21 C24 . . . 122.5(3) no
C20 C21 C22 . . . 124.2(3) no
C20 C21 C24 . . . 113.3(3) no
N6 C22 C23 . . . 115.8(3) no
N6 C22 C21 . . . 119.1(3) no
C21 C22 C23 . . . 125.1(3) no
O2 C23 C22 . . . 117.7(3) no
O2 C23 O3 . . . 126.5(3) no
O3 C23 C22 . . . 115.8(3) no
S2 C24 C21 . . . 112.5(2) no
S2 C25 N4 . . . 126.6(3) no
S2 C25 S3 . . . 119.5(2) no
S3 C25 N4 . . . 114.0(3) no
S3 C26 C27 . . . 122.4(3) no
S3 C26 N5 . . . 113.6(3) no
N5 C26 C27 . . . 124.0(4) no
N6 C28 C29 . . . 87.8(2) no
S1 C28 C29 . . . 116.3(2) no
S1 C28 N6 . . . 109.8(2) no
N7 C29 C28 . . . 121.0(3) no
N7 C29 C30 . . . 119.8(3) no
C28 C29 C30 . . . 85.1(3) no
O4 C30 N6 . . . 132.0(3) no
N6 C30 C29 . . . 91.0(3) no
O4 C30 C29 . . . 137.0(3) no
O5 C31 C32 . . . 120.9(3) no
O5 C31 N7 . . . 123.9(3) no
N7 C31 C32 . . . 115.2(3) no
N8 C32 C31 . . . 110.4(3) no
N8 C33 N11 . . . 109.4(4) no
S1 C20 H20A . . . 108.00 no
S1 C20 H20B . . . 108.00 no
C21 C20 H20A . . . 108.00 no
C21 C20 H20B . . . 108.00 no
H20A C20 H20B . . . 107.00 no
S2 C24 H24A . . . 109.00 no
S2 C24 H24B . . . 109.00 no
C21 C24 H24A . . . 109.00 no
C21 C24 H24B . . . 109.00 no
H24A C24 H24B . . . 108.00 no
C26 C27 H27A . . . 109.00 no
C26 C27 H27B . . . 109.00 no
C26 C27 H27C . . . 110.00 no
H27A C27 H27B . . . 109.00 no
H27A C27 H27C . . . 109.00 no
H27B C27 H27C . . . 109.00 no
S1 C28 H28 . . . 113.00 no
N6 C28 H28 . . . 113.00 no
C29 C28 H28 . . . 113.00 no
N7 C29 H29 . . . 110.00 no
C28 C29 H29 . . . 110.00 no
C30 C29 H29 . . . 110.00 no
N8 C32 H32A . . . 110.00 no
N8 C32 H32B . . . 110.00 no
C31 C32 H32A . . . 110.00 no
C31 C32 H32B . . . 110.00 no
H32A C32 H32B . . . 108.00 no
N8 C33 H33 . . . 125.00 no
N11 C33 H33 . . . 125.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C20 . . 1.805(4) no
S1 C28 . . 1.797(4) no
S2 C24 . . 1.815(4) no
S2 C25 . . 1.742(4) no
S3 C26 . . 1.733(4) no
S3 C25 . . 1.732(4) no
O1 C15 . . 1.425(5) no
O1 C14 . . 1.350(5) no
O2 C23 . . 1.243(5) no
O3 C23 . . 1.247(4) no
O4 C30 . . 1.197(4) no
O5 C31 . . 1.217(4) no
N1 N2 . . 1.382(5) no
N1 C14 . . 1.310(5) no
N2 C7 . . 1.448(5) no
N2 C6 . . 1.351(5) no
N3 C17 . . 1.506(5) no
N3 C18 . . 1.473(6) no
N3 C19 . . 1.472(5) no
N3 H3N . . 0.96(4) no
N4 N5 . . 1.392(4) no
N4 C25 . . 1.292(5) no
N5 C26 . . 1.288(5) no
N6 C28 . . 1.466(4) no
N6 C30 . . 1.385(4) no
N6 C22 . . 1.400(4) no
N7 C31 . . 1.338(4) no
N7 C29 . . 1.430(5) no
N8 N9 . . 1.325(5) no
N8 C33 . . 1.320(5) no
N8 C32 . . 1.454(5) no
N9 N10 . . 1.279(6) no
N10 N11 . . 1.348(7) no
N11 C33 . . 1.307(6) no
N7 H7N . . 0.8600 no
C1 C14 . . 1.406(5) no
C1 C2 . . 1.396(5) no
C1 C6 . . 1.393(5) no
C2 C3 . . 1.351(7) no
C3 C4 . . 1.397(7) no
C4 C5 . . 1.368(6) no
C5 C6 . . 1.399(5) no
C7 C8 . . 1.501(5) no
C8 C9 . . 1.384(6) no
C8 C13 . . 1.380(5) no
C9 C10 . . 1.374(6) no
C10 C11 . . 1.368(6) no
C11 C12 . . 1.365(6) no
C12 C13 . . 1.378(6) no
C15 C16 . . 1.489(6) no
C16 C17 . . 1.461(6) no
C2 H2 . . 0.9300 no
C3 H3 . . 0.9300 no
C4 H4 . . 0.9300 no
C5 H5 . . 0.9300 no
C7 H7B . . 0.9700 no
C7 H7A . . 0.9700 no
C9 H9 . . 0.9300 no
C10 H10 . . 0.9300 no
C11 H11 . . 0.9300 no
C12 H12 . . 0.9300 no
C13 H13 . . 0.9300 no
C15 H15B . . 0.9700 no
C15 H15A . . 0.9700 no
C16 H16A . . 0.9700 no
C16 H16B . . 0.9700 no
C17 H17A . . 0.9700 no
C17 H17B . . 0.9700 no
C18 H18B . . 0.9600 no
C18 H18A . . 0.9600 no
C18 H18C . . 0.9600 no
C19 H19C . . 0.9600 no
C19 H19B . . 0.9600 no
C19 H19A . . 0.9600 no
C20 C21 . . 1.515(5) no
C21 C24 . . 1.496(5) no
C21 C22 . . 1.339(5) no
C22 C23 . . 1.524(5) no
C26 C27 . . 1.491(6) no
C28 C29 . . 1.548(5) no
C29 C30 . . 1.540(5) no
C31 C32 . . 1.510(5) no
C20 H20A . . 0.9700 no
C20 H20B . . 0.9700 no
C24 H24A . . 0.9700 no
C24 H24B . . 0.9700 no
C27 H27A . . 0.9600 no
C27 H27B . . 0.9600 no
C27 H27C . . 0.9600 no
C28 H28 . . 0.9800 no
C29 H29 . . 0.9800 no
C32 H32A . . 0.9700 no
C32 H32B . . 0.9700 no
C33 H33 . . 0.9300 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3N O3 1_546 0.96(4) 1.70(4) 2.660(4) 174(3) yes
N7 H7N O2 1_545 0.8600 2.0200 2.868(3) 167.00 yes
C18 H18C O4 1_556 0.9600 2.5200 3.303(5) 139.00 yes
C24 H24A N4 . 0.9700 2.4100 2.961(5) 116.00 yes
C24 H24B O3 . 0.9700 2.3800 2.882(4) 112.00 yes
C32 H32A O2 2_546 0.9700 2.2800 3.218(4) 164.00 yes
C32 H32B O2 1_545 0.9700 2.5000 3.318(4) 142.00 yes
C19 H19B CgA . 0.96 2.91 3.869(6) 174 yes
C20 H20B CgD . 0.97 2.72 3.642(4) 158 yes
C29 H29 CgA 1_545 0.98 2.99 3.861(4) 149 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C20 S1 C28 C29 . . . . 155.3(3) no
C20 S1 C28 N6 . . . . 57.8(3) no
C28 S1 C20 C21 . . . . -47.1(3) no
C24 S2 C25 N4 . . . . 12.6(4) no
C24 S2 C25 S3 . . . . -167.0(2) no
C25 S2 C24 C21 . . . . -111.3(3) no
C25 S3 C26 C27 . . . . -179.3(3) no
C26 S3 C25 N4 . . . . -0.1(3) no
C25 S3 C26 N5 . . . . -0.4(3) no
C26 S3 C25 S2 . . . . 179.6(2) no
C14 O1 C15 C16 . . . . -176.1(3) no
C15 O1 C14 C1 . . . . 171.1(3) no
C15 O1 C14 N1 . . . . -8.4(5) no
N2 N1 C14 C1 . . . . 1.4(4) no
C14 N1 N2 C7 . . . . -175.3(3) no
N2 N1 C14 O1 . . . . -179.0(3) no
C14 N1 N2 C6 . . . . -1.9(4) no
N1 N2 C6 C5 . . . . -177.3(4) no
C7 N2 C6 C5 . . . . -4.6(7) no
N1 N2 C7 C8 . . . . -102.2(4) no
C6 N2 C7 C8 . . . . 85.6(5) no
C7 N2 C6 C1 . . . . 174.5(3) no
N1 N2 C6 C1 . . . . 1.7(4) no
C19 N3 C17 C16 . . . . -164.0(4) no
C18 N3 C17 C16 . . . . 74.5(5) no
C25 N4 N5 C26 . . . . -0.7(4) no
N5 N4 C25 S3 . . . . 0.4(4) no
N5 N4 C25 S2 . . . . -179.2(3) no
N4 N5 C26 S3 . . . . 0.6(4) no
N4 N5 C26 C27 . . . . 179.6(3) no
C30 N6 C22 C21 . . . . -133.6(4) no
C30 N6 C22 C23 . . . . 49.7(5) no
C28 N6 C22 C23 . . . . -167.3(3) no
C30 N6 C28 C29 . . . . -11.3(3) no
C22 N6 C28 S1 . . . . -48.2(4) no
C22 N6 C28 C29 . . . . -165.4(3) no
C22 N6 C30 O4 . . . . -16.5(7) no
C28 N6 C22 C21 . . . . 9.4(5) no
C30 N6 C28 S1 . . . . 106.0(2) no
C22 N6 C30 C29 . . . . 161.9(4) no
C28 N6 C30 O4 . . . . -167.1(4) no
C28 N6 C30 C29 . . . . 11.3(3) no
C29 N7 C31 O5 . . . . -1.4(5) no
C31 N7 C29 C30 . . . . -145.3(3) no
C29 N7 C31 C32 . . . . 176.6(3) no
C31 N7 C29 C28 . . . . 111.5(4) no
N9 N8 C32 C31 . . . . -69.8(4) no
N9 N8 C33 N11 . . . . -0.1(4) no
C32 N8 C33 N11 . . . . -177.9(3) no
C33 N8 N9 N10 . . . . 0.0(4) no
C32 N8 N9 N10 . . . . 178.1(4) no
C33 N8 C32 C31 . . . . 107.8(4) no
N8 N9 N10 N11 . . . . 0.1(5) no
N9 N10 N11 C33 . . . . -0.1(5) no
N10 N11 C33 N8 . . . . 0.2(5) no
C2 C1 C6 N2 . . . . -176.6(3) no
C2 C1 C6 C5 . . . . 2.6(6) no
C14 C1 C2 C3 . . . . -175.0(4) no
C14 C1 C6 C5 . . . . 178.4(3) no
C2 C1 C14 O1 . . . . -5.2(7) no
C14 C1 C6 N2 . . . . -0.8(4) no
C6 C1 C2 C3 . . . . -0.9(6) no
C6 C1 C14 N1 . . . . -0.5(4) no
C2 C1 C14 N1 . . . . 174.4(4) no
C6 C1 C14 O1 . . . . 179.9(3) no
C1 C2 C3 C4 . . . . -1.7(7) no
C2 C3 C4 C5 . . . . 2.7(7) no
C3 C4 C5 C6 . . . . -1.0(6) no
C4 C5 C6 C1 . . . . -1.6(6) no
C4 C5 C6 N2 . . . . 177.3(4) no
N2 C7 C8 C9 . . . . 48.2(5) no
N2 C7 C8 C13 . . . . -134.6(4) no
C7 C8 C13 C12 . . . . -176.7(4) no
C9 C8 C13 C12 . . . . 0.6(6) no
C13 C8 C9 C10 . . . . -1.1(6) no
C7 C8 C9 C10 . . . . 176.1(4) no
C8 C9 C10 C11 . . . . 1.1(6) no
C9 C10 C11 C12 . . . . -0.5(7) no
C10 C11 C12 C13 . . . . 0.0(7) no
C11 C12 C13 C8 . . . . 0.0(6) no
O1 C15 C16 C17 . . . . 59.5(5) no
C15 C16 C17 N3 . . . . -173.0(4) no
S1 C20 C21 C22 . . . . 19.2(5) no
S1 C20 C21 C24 . . . . -163.3(2) no
C20 C21 C22 N6 . . . . 6.9(5) no
C20 C21 C22 C23 . . . . -176.7(3) no
C20 C21 C24 S2 . . . . 81.3(3) no
C22 C21 C24 S2 . . . . -101.2(4) no
C24 C21 C22 N6 . . . . -170.3(3) no
C24 C21 C22 C23 . . . . 6.0(6) no
N6 C22 C23 O2 . . . . 32.8(5) no
C21 C22 C23 O3 . . . . 37.0(5) no
N6 C22 C23 O3 . . . . -146.5(3) no
C21 C22 C23 O2 . . . . -143.7(4) no
S1 C28 C29 N7 . . . . 21.1(4) no
S1 C28 C29 C30 . . . . -100.9(3) no
N6 C28 C29 N7 . . . . 132.1(3) no
N6 C28 C29 C30 . . . . 10.1(2) no
N7 C29 C30 O4 . . . . 44.4(6) no
N7 C29 C30 N6 . . . . -133.9(3) no
C28 C29 C30 O4 . . . . 167.5(5) no
C28 C29 C30 N6 . . . . -10.7(3) no
O5 C31 C32 N8 . . . . -38.1(5) no
N7 C31 C32 N8 . . . . 143.9(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655945
